WO2021167074A1 - Composé contenant un groupe photoréactif, polymère et film de retard - Google Patents

Composé contenant un groupe photoréactif, polymère et film de retard Download PDF

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WO2021167074A1
WO2021167074A1 PCT/JP2021/006403 JP2021006403W WO2021167074A1 WO 2021167074 A1 WO2021167074 A1 WO 2021167074A1 JP 2021006403 W JP2021006403 W JP 2021006403W WO 2021167074 A1 WO2021167074 A1 WO 2021167074A1
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carbon atoms
atom
substituent
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竜一 坂下
範武 村上
洋樹 一條
優輝 七田
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東ソー株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/19—Hydroxy compounds containing aromatic rings
    • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • the present invention relates to a compound containing a photoreactive group. More specifically, the present invention relates to a polymer of a compound containing a photoreactive group and a retardation film containing the same.
  • Optical thin films such as retardation films are used in various image display devices from the viewpoint of expanding the viewing angle.
  • a thin film formed by stretching a resin is known, and examples of the material include polycarbonate resin, cyclic polyolefin, cellulose acylate and the like (see, for example, Patent Documents 1 to 3).
  • the stretched film has problems such as easy cracking and light leakage due to residual stress strain.
  • it has been proposed to use an optically anisotropic layer using a liquid crystal compound instead of the stretched birefringent film.
  • the present invention has been made in view of the above problems, and an object of the present invention is to align without the occurrence of cracks or the like derived from the processing history and without the need for an alignment film, and to exhibit a sufficient phase difference.
  • the purpose is to provide an optical thin film.
  • the present inventor has solved the above problems by using a compound containing a photoreactive group having a specific structure as a polymer containing the compound. We have found that a sufficient phase difference can be exhibited and can be used for optical applications such as viewing angle compensation, and have completed the present invention.
  • X 1 to X 3 may independently have an aromatic ring having 5 to 7 carbon atoms or a substituent may have a substituent, and 5 to 7 carbon atoms may have a substituent.
  • X 1 to X 3 may independently have an aromatic ring having 5 to 7 carbon atoms or a substituent may have a substituent, and 5 to 7 carbon atoms may have a substituent.
  • the substituents in 1 to X 3 independently represent one of a group consisting of a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and X 1 to X 3 are substituents.
  • the hydrogen atoms Y 1 and Y 2 each independently represent one of a group consisting of a hydroxy group, a carboxyl group, and an amino group.
  • Ar 1 and Ar 2 are independent, respectively. It represents an aromatic ring having 5 to 7 carbon atoms which may have a substituent, and any carbon atom in the aromatic ring may be substituted with a nitrogen atom, an oxygen atom, or a sulfur atom, where Ar 1 and Ar.
  • the substituent in Ar 2 independently represents one of a group consisting of a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and Ar 1 and Ar 2 have a substituent. If not, it is a hydrogen atom.
  • R 1 to R 4 are independently composed of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms.
  • L 1 and L 4 each independently represent one of the groups consisting of a single bond or -O-, -NR 5- , where R 5 is a hydrogen atom or the number of carbon atoms.
  • L 2 and L 3 are independently single-bonded or -O-, -CO-O-, -CO-NR 6- , -CO-, respectively.
  • -CR 7 R 8 -. represents one of the group consisting of wherein, .R 7 and R 8 R 6 represents one of the group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms are each independently Represents one of a group consisting of a hydrogen atom, a halogen atom or an alkyl group having 1 to 5 carbon atoms.
  • a and b independently represent 0 or 1 respectively.
  • X 1 to X 3 may independently have an aromatic ring having 5 to 7 carbon atoms or a substituent may have a substituent, or 5 to 7 carbon atoms may have a substituent.
  • X 1 to X 3 may independently have an aromatic ring having 5 to 7 carbon atoms or a substituent may have a substituent, or 5 to 7 carbon atoms may have a substituent.
  • the substituents in 1 to X 3 independently represent one of a group consisting of a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and X 1 to X 3 are substituents.
  • .Y 3 and Y 4 is a hydrogen atom, each independently, -O -, - CO -, - NR 9 -. represents one of the group consisting of wherein, R 9 is hydrogen Represents one of a group consisting of an atom or an alkyl group having 1 to 5 carbon atoms.
  • Ar 1 and Ar 2 each independently represent an aromatic ring having 5 to 7 carbon atoms which may have a substituent.
  • any carbon atom in the aromatic ring may be substituted with a nitrogen atom, an oxygen atom, and a sulfur atom.
  • the substituents in Ar 1 and Ar 2 are independently halogen atoms and having 1 to 5 carbon atoms, respectively. It represents one of a group consisting of an alkyl group and an alkoxy group having 1 to 5 carbon atoms, and when Ar 1 and Ar 2 do not have a substituent, it is a hydrogen atom.
  • R 1 to R 4 independently represent one of a group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms.
  • L 1 and L 4 represent one of a group consisting of a single bond or -O-, -NR 5-.
  • R 5 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • L 2 and L 3 is a single bond or -O -, - CO-O - , - CO-NR 6 -, - CO -, - represents one of the group consisting of - CR 7 R 8.
  • R 6 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 7 and R 8 each independently represent one of a group consisting of a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.
  • a and b independently represent 0 or 1, respectively.
  • Y 5 and Y 6 each independently represent one of a group consisting of -O-, -CO-, and -NR 10- , where R 10 is a hydrogen atom or the number of carbon atoms.
  • .X 4 ⁇ X 6 representing one of the group consisting of alkyl groups having 1 to 5 independently, have an aromatic ring or a substituent of 1-7 carbon atoms 5 may have a substituent Represents any of an alicyclic hydrocarbon group having 5 to 7 carbon atoms, and any carbon atom in the aromatic ring or the alicyclic hydrocarbon group is replaced with a nitrogen atom, an oxygen atom, or a sulfur atom.
  • R 11 and R 12 represent one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • C represents 0 or 1).
  • Y 7 and Y 8 are each independently, -O -, - CO -, - NR 13 -.
  • R 13 is a hydrogen atom or a carbon atoms
  • Z represents an alicyclic hydrocarbon group having 5 to 7 carbon atoms, a linear alkylene group having 2 to 20 carbon atoms, and 4 to 20 carbon atoms.
  • another aspect of the present invention has the structural unit D represented by the following formula (5), and the structural unit B represented by the formula (3) or the structural unit C represented by the formula (4). It relates to a polymer having at least one of them.
  • Y 9 and Y 10 are each independently a single bond or -O -, - CO -, - NR 14 -. Represents one of the group consisting of wherein, R 14 is a hydrogen atom Alternatively, it represents one of a group consisting of alkyl groups having 1 to 5 carbon atoms.
  • Ar 3 and Ar 4 each independently represent an aromatic ring having 5 to 7 carbon atoms which may have a substituent.
  • R 15 to R 18 are independently hydrogen atom, halogen atom, cyano group, nitro group, and carbon number 1.
  • alkyl group 1-5, the .L 5 which represents one of the group consisting of an alkoxy group having 1 to 5 carbon atoms, a single bond or -O -, - NR 25 -. represents one of the group consisting of wherein, R 25 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • D to f independently represent 0 or 1 respectively.
  • Another aspect of the present invention relates to an optical thin film containing the polymer.
  • Another aspect of the present invention relates to a retardation film provided with the thin film. Furthermore, another aspect of the present invention relates to a liquid crystal alignment film provided with the thin film.
  • an optical thin film exhibiting excellent liquid crystal alignment and a retardation film composed of the same by irradiation with polarized ultraviolet rays or obliquely incident ultraviolet rays, and heat treatment without the need for an alignment film.
  • One aspect of the present invention is a compound represented by the above formula (1) containing a photoreactive group (hereinafter referred to as "the compound of the present invention”).
  • a photoreactive group is a group that produces an orientation ability when irradiated with light. Specifically, irradiation with light causes a photoreaction that is the origin of orientation ability, such as a molecular dimerization reaction, an isomerization reaction, a photocrosslinking reaction, and a photodecomposition reaction.
  • the photoreactive group preferably has an unsaturated bond, particularly a double bond.
  • Azobenzene group, azonaphthalene group, aromatic heterocyclic azo group, bisazo group, formazan group, and groups having a basic structure of azoxybenzene are exemplified.
  • the cinnamoyl group is preferable from the viewpoint that the amount of light irradiation required for photo-orientation is relatively small and the thermal stability and the stability over time are excellent.
  • X 1 to X 3 independently have an aromatic ring having 5 to 7 carbon atoms which may have a substituent or an aromatic ring having 5 to 7 carbon atoms which may have a substituent. It represents any of the alicyclic hydrocarbon groups, and any carbon atom in the aromatic ring or in the alicyclic hydrocarbon group may be substituted with a nitrogen atom, an oxygen atom or a sulfur atom.
  • substituents in X 1 to X 3 include a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and X 1 to X 3 do not have a substituent. If it is a hydrogen atom.
  • X 1 to X 3 are preferably one of a group consisting of a benzene ring, a methylbenzene ring, a t-butylbenzene ring, a dimethylbenzene ring, a tetrafluorobenzene ring or a cyclohexane ring, and more preferably a trans-cyclohexane ring.
  • Y 1 and Y 2 each independently represent one of a group consisting of a hydroxy group, a carboxyl group, and an amino group.
  • Y 1 and Y 2 are preferably hydroxy groups.
  • Ar 1 and Ar 2 each independently represent an aromatic ring having 5 to 7 carbon atoms which may have a substituent, and any carbon atom in the aromatic ring can be a nitrogen atom, an oxygen atom, or a sulfur atom. It may be replaced.
  • substituents in Ar 1 and Ar 2 include a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and Ar 1 and Ar 2 do not have a substituent. If it is a hydrogen atom.
  • Ar 1 and Ar 2 are preferably benzene rings which may have a substituent, and more preferably benzene rings.
  • R 1 to R 4 independently represent one of a group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms.
  • R 1 to R 4 are preferably a hydrogen atom or a cyano group, and more preferably a hydrogen atom.
  • L 1 and L 4 each independently represent a single bond or one of a group consisting of -O- and -NR 5-.
  • L 1 and L 4 are preferably -O- or -NR 5- .
  • R 5 in L 1 and L 4 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the alkyl group of 1 to 5 carbon atoms for R 5, include methyl group, ethyl group, propyl group, butyl group, a pentyl group.
  • L 2 and L 3 is independently a single bond or -O -, - CO-O - , - CO-NR 6 -, - CO -, - represents one of the group consisting of - CR 7 R 8. However, the left-right relationship of L 2 and L 3 may be reversed.
  • L 2 and L 3 are preferably single-bonded or -CO-NR 6- , more preferably single-bonded.
  • R 6 in L 2 and L 3 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Examples of the alkyl group having 1 to 5 carbon atoms in R 6 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • R 7 and R 8 in L 2 and L 3 independently represent one of a group consisting of a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.
  • Examples of the halogen atom in R 7 and R 8 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the alkyl group having 1 to 5 carbon atoms in R 7 and R 8 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • a and b independently represent 0 or 1, respectively.
  • the compound represented by the formula (1) is preferably a compound represented by the following formula (11).
  • X 1 to X 3 , Ar 1 , Ar 2 , R 1 to R 4 , L 1 to L 4 , a, and b are the same as those in the formula (1).
  • the compound represented by the formula (1) is more preferably a compound represented by the following formula (12).
  • X 7 and X 8 each independently have an aromatic ring having 5 to 7 carbon atoms which may have a substituent or an aromatic ring having 5 to 7 carbon atoms which may have a substituent.
  • examples of the substituents in X 7 and X 8 include a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and X 7 and X 8 do not have a substituent. If it is a hydrogen atom.
  • X 7 and X 8 is preferably one of the group consisting of benzene ring, methylbenzene ring, t- butyl benzene ring, dimethyl benzene ring or a cyclohexane ring, even more preferably either benzene ring or a cyclohexane ring .
  • X 7 is preferably either an aromatic ring having 5 to 7 carbon atoms having no substituent or an alicyclic hydrocarbon group having 5 to 7 carbon atoms having no substituent.
  • L 6 represents a single bond or -O -, - CO-O - , - CO-NR 21 -, - CO -, - represents one of the group consisting of - CR 22 R 23.
  • L 6 is preferably a single bond.
  • R 21 in L 6 represents either a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group having 1 to 5 carbon atoms in R 21 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • R 22 and R 23 in L 6 each independently represent one of a group consisting of a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms. However, the left-right relationship of L 6 may be reversed.
  • the halogen atom in R 22 and R 23 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the alkyl group having 1 to 5 carbon atoms in R 22 and R 23 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • R 19 and R 20 each independently form one of a group consisting of a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. show.
  • Examples of the alkyl group having 1 to 5 carbon atoms in R 19 and R 20 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • alkoxy group having 1 to 5 carbon atoms in R 19 and R 20 examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
  • n 1 and n 2 each independently represent an integer of 0 to 4.
  • the ester bond in the formula (12) may be independently replaced with an amide bond which may have a substituent.
  • substituents include a halogen atom and an alkyl group having 1 to 5 carbon atoms.
  • the compound of the present invention is more preferably a compound represented by the following formula (13).
  • Y 11 represents one of a group consisting of a benzene ring, a biphenyl ring, a cyclohexane ring, and a bicyclohexane ring which may have a substituent.
  • R 19 and R 20 are independent of each other.
  • N 1 and n 2 each independently represent an integer of 0 to 4.
  • Y 11 represents one of a group consisting of a benzene ring, a biphenyl ring, a cyclohexane ring, and a bicyclohexane ring which may have a substituent.
  • substituents in Y 11 include a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and when Y 11 does not have a substituent, it is a hydrogen atom.
  • Y 11 is preferably one of a group consisting of a benzene ring, a biphenyl ring and a cyclohexane ring which may have a substituent, and more preferably a benzene ring, a methylbenzene ring, a t-butylbenzene ring and a tetra. It is one of a group consisting of a methylbiphenyl ring and a cyclohexane ring.
  • Examples of the alkyl group having 1 to 5 carbon atoms in R 19 and R 20 include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • Examples of the alkoxy group having 1 to 5 carbon atoms in R 19 and R 20 include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
  • the ester bond in the formula (13) may be independently replaced with an amide bond which may have a substituent.
  • substituents include a halogen atom and an alkyl group having 1 to 5 carbon atoms.
  • the compounds of the present invention can be synthesized by combining common techniques in synthetic organic chemistry. For example, as a method for synthesizing a compound represented by the formula (1) in which Y 1 and Y 2 are hydroxy groups, the hydroxy group is protected (synthesis scheme A1) as shown in the following synthesis scheme, and then the hydroxy group is used. A method of subjecting a dihydroxy compound or an amine compound to a condensation reaction (synthesis scheme A2) and deprotecting the compound (synthesis scheme A3) can be exemplified.
  • the protecting group PG used in the synthesis scheme is not particularly limited.
  • the substituted methyl ether protecting group includes a methoxymethyl group, a methylthiomethyl group, a benzyloxymethyl group, a t-butoxymethyl group, a 4-pentenyloxymethyl group, a tetrahydropyranyl group, a tetrahydrofuranyl group, and a tetrahydrothio.
  • a furanyl group is exemplified.
  • Examples of the substituted ethyl ether protecting group include 1-ethoxyethyl group, 1- (2-chloroethoxy) ethyl group, 2-hydroethyl group, 2-bromoethyl group, t-butyl group, cyclohexyl group and benzyl group.
  • Examples of the methoxy-substituted benzyl ether protective group include p-methoxybenzyl group, 3,4-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, p-phenylbenzyl group, p-cyanobenzyl group, diphenylmethyl group and 4-methoxy.
  • the silyl ether protecting group includes a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a dimethylisopropylsilyl group, a t-butyldimethylsilyl group, a tribenzylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group and t-butylmethoxy.
  • Examples thereof include a phenylsilyl group and a t-butoxydiphenylsilyl group. Of these, a tetrahydropyranyl group or a t-butyldimethylsilyl group is particularly preferable from the viewpoint of cost and convenience.
  • the condensing agent used in the condensation reaction in the synthesis scheme A2 is not particularly limited.
  • examples of the carbodiimide condensing agent include 1,3-bis (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) carbodiimide, N, N'-diisopropylcarbodiimide, and N, N'-dicyclohexylcarbodiimide.
  • N, N'-di-t-butylcarbodiimide, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide are exemplified.
  • ester condensing agent examples include N-hydroxysuccinimide, bis (2-oxo-3-oxazolidinylphosphinic acid chloride, bis (pentafluorophenyl) carbonate, isobutyl chlorophosphate, 4-nitrophenyl chlorophosphate, and chloride chloride.
  • Examples of the phosgene condensing agent are thiocarbonyl. Examples include chloride, carbonic acid (trichloromethyl), and O, O'-di-2-pyridyl thiocarbonate. Examples of the triflate condensing agent include 2- [N, N'-bis (trifluoromethanesulfonyl) amino] -5. Examples thereof include chloropyridine, 4-nitrophenyl trifluoromethanesulfonic acid, and N-phenylbis (trifluoromethanesulfonimide). Of these, N, N'-dicyclohexylcarbodiimide and 1-, in particular, from the viewpoint of cost and convenience. (3-Dimethylaminopropyl) -3-ethylcarbodiimide, 1,1'-carbonyldiimidazole is preferred.
  • the method used for deprotection in the synthetic scheme A3 is not particularly limited. A deprotection method suitable for the protecting group used may be used.
  • the protecting group PG used in the synthesis scheme is not particularly limited.
  • the substituted methyl ether protecting group includes a methoxymethyl group, a methylthiomethyl group, a benzyloxymethyl group, a t-butoxymethyl group, a 4-pentenyloxymethyl group, a tetrahydropyranyl group, a tetrahydrofuranyl group, and a tetrahydrothio.
  • a furanyl group is exemplified.
  • Examples of the substituted ethyl ether protecting group include 1-ethoxyethyl group, 1- (2-chloroethoxy) ethyl group, 2-hydroethyl group, 2-bromoethyl group, t-butyl group, cyclohexyl group and benzyl group.
  • Examples of the methoxy-substituted benzyl ether protective group include p-methoxybenzyl group, 3,4-dimethoxybenzyl group, 2,6-dimethoxybenzyl group, p-phenylbenzyl group, p-cyanobenzyl group, diphenylmethyl group and 4-methoxy.
  • the silyl ether protecting group includes a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a dimethylisopropylsilyl group, a t-butyldimethylsilyl group, a tribenzylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group and t-butylmethoxy.
  • Examples thereof include a phenylsilyl group and a t-butoxydiphenylsilyl group. Of these, a tetrahydropyranyl group or a t-butyldimethylsilyl group is particularly preferable from the viewpoint of cost and convenience.
  • the condensing agent used in the condensation reaction in the synthesis scheme A5 is not particularly limited.
  • examples of the carbodiimide condensing agent include 1,3-bis (2,2-dimethyl-1,3-dioxolan-4-ylmethyl) carbodiimide, N, N'-diisopropylcarbodiimide, and N, N'-dicyclohexylcarbodiimide.
  • N, N'-di-t-butylcarbodiimide, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide are exemplified.
  • ester condensing agent examples include N-hydroxysuccinimide, bis (2-oxo-3-oxazolidinylphosphinic acid chloride, bis (pentafluorophenyl) carbonate, isobutyl chlorophosphate, 4-nitrophenyl chlorogeate, and chloride chloride.
  • Examples of the phosgen condensing agent are thiocarbonyl. Examples include chloride, carbonate (trichloromethyl), and O, O'-di-2-pyridyl thiocarbonate. Examples of the trifurate condensing agent include 2- [N, N'-bis (trifluoromethanesulfonyl) amino] -5. Examples thereof include chloropyridine, 4-nitrophenyl trifluoromethanesulfonic acid, and N-phenylbis (trifluoromethanesulfonimide). Of these, N, N'-dicyclohexylcarbodiimide and 1-, in particular, from the viewpoint of cost and convenience. (3-Dimethylaminopropyl) -3-ethylcarbodiimide is preferred.
  • the method used for deprotection in the synthetic scheme A6 is not particularly limited. A deprotection method suitable for the protecting group used may be used.
  • the present invention has a structural unit A represented by the following formula (2), a structural unit B represented by the following formula (3), or a configuration represented by the following formula (4).
  • a polymer having at least one of the units C (hereinafter referred to as "polymer 1 of the present invention") can be mentioned.
  • the polymer 1 of the present invention is preferably a polymer having a structural unit A represented by the formula (2) and a structural unit B represented by the formula (3).
  • X 1 to X 3 may independently have an aromatic ring having 5 to 7 carbon atoms or a substituent may have a substituent, or 5 to 7 carbon atoms may have a substituent.
  • the substituents in 1 to X 3 independently represent one of a group consisting of a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and X 1 to X 3 are substituents. If no, .Y 3 and Y 4 is a hydrogen atom, each independently, -O -, - CO -, - NR 9 -.
  • R 9 is hydrogen
  • R 9 represents one of a group consisting of an atom or an alkyl group having 1 to 5 carbon atoms.
  • Ar 1 and Ar 2 each independently represent an aromatic ring having 5 to 7 carbon atoms which may have a substituent. Any carbon atom in the aromatic ring may be substituted with a nitrogen atom, an oxygen atom, and a sulfur atom.
  • the substituents in Ar 1 and Ar 2 are independently halogen atoms and having 1 to 5 carbon atoms, respectively. It represents one of a group consisting of an alkyl group and an alkoxy group having 1 to 5 carbon atoms, and when Ar 1 and Ar 2 do not have a substituent, it is a hydrogen atom.
  • R 1 to R 4 independently represent one of a group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms.
  • L 1 and L 4 represent one of a group consisting of a single bond or -O-, -NR 5-.
  • R 5 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • L 2 and L 3 is a single bond or -O -, - CO-O - , - CO-NR 6 -, - CO -, - represents one of the group consisting of - CR 7 R 8.
  • R 6 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • R 7 and R 8 each independently represent one of a group consisting of a hydrogen atom, a halogen atom, or an alkyl group having 1 to 5 carbon atoms.
  • a and b independently represent 0 or 1, respectively.
  • Y 5 and Y 6 each independently represent one of a group consisting of -O-, -CO-, and -NR 10- , where R 10 is a hydrogen atom or the number of carbon atoms.
  • .X 4 ⁇ X 6 representing one of the group consisting of alkyl groups having 1 to 5 independently, have an aromatic ring or a substituent of 1-7 carbon atoms 5 may have a substituent Represents any of an alicyclic hydrocarbon group having 5 to 7 carbon atoms, and any carbon atom in the aromatic ring or the alicyclic hydrocarbon group is replaced with a nitrogen atom, an oxygen atom, or a sulfur atom.
  • R 11 and R 12 represent one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • C represents 0 or 1).
  • Y 7 and Y 8 are each independently, -O -, - CO -, - NR 13 -.
  • R 13 is a hydrogen atom or a carbon atoms
  • Z represents an alicyclic hydrocarbon group having 5 to 7 carbon atoms, a linear alkylene group having 2 to 20 carbon atoms, and 4 to 20 carbon atoms. Represents a type of group consisting of branched alkylene groups.
  • X 1 to X 3 , Ar 1 , Ar 2 , R 1 to R 4 , L 1 to L 4 , a and b are the same as those in the formula (1).
  • Y 3 and Y 4 each independently, -O -, - CO -, - represents one of the group consisting of - NR 9.
  • R 9 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Y 3 and Y 4 are preferably —O—.
  • Y 5 and Y 6 independently represent one of a group consisting of -O-, -CO-, and -NR 10-.
  • R 10 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Y 5 and Y 6 are preferably —O— or ⁇ CO—.
  • X 4 - X 6 are each independently, an alicyclic hydrocarbon group having an aromatic ring or carbon atoms which may have a substituent 5-7 have 1-5 carbon atoms which may 7 have a substituent Any carbon atom in the aromatic ring or the alicyclic hydrocarbon group may be substituted with a nitrogen atom, an oxygen atom, or a sulfur atom.
  • X 4 ⁇ X 6 is no substituent If it is a hydrogen atom.
  • X 4 ⁇ X 6 is preferably a benzene ring, methylbenzene ring, t- butyl benzene ring, dimethyl benzene ring, a one of the group consisting of tetrafluoroethylene benzene ring or a cyclohexane ring, more preferably a benzene ring or a trans- It is a cyclohexane ring.
  • R 11 and R 12 represent one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • the alkyl group of 1 to 5 carbon atoms for R 5, include methyl group, ethyl group, propyl group, butyl group, a pentyl group.
  • c represents 0 or 1.
  • Y 7 and Y 8 are each independently, -O -, - CO -, - represents one of the group consisting of - NR 13.
  • R 13 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Y 7 and Y 8 are preferably ⁇ CO ⁇ .
  • Z represents a kind of a group consisting of an alicyclic hydrocarbon group having 5 to 7 carbon atoms, a linear alkylene group having 2 to 20 carbon atoms, and a branched alkylene group having 4 to 20 carbon atoms.
  • Z is preferably an alicyclic hydrocarbon group having 5 to 7 carbon atoms, a linear alkylene group having 2 to 20 carbon atoms, and more preferably an alicyclic hydrocarbon group having 5 to 7 carbon atoms or carbon. It is a linear alkylene group having a number of 2 to 10.
  • Polymer 1 of the present invention is preferably a polymer having a structural unit A 1 comprising a cinnamoyl group represented by the following formula (14), the constitutional unit C 1 represented by the following formula (15) be.
  • X 7 and X 8 independently, - aromatic ring or carbon atoms which may have a substituent 5 have 1-5 carbon atoms which may 7 substituted 7 the .
  • L 6 represent either a alicyclic hydrocarbon group, a single bond or -O -, - CO-O - , - CO-NR 21 -, - CO -, - CR 22 R 23 - group consisting of
  • R 21 represents either a hydrogen atom or an alkyl group having 1 to 5 carbon atoms .
  • R 22 and R 23 independently represent a hydrogen atom, a halogen atom or 1 to 5 carbon atoms, respectively. Represents one of a group consisting of 5 alkyl groups. M and l each independently represent 0 or 1. R 19 and R 20 independently represent a hydrogen atom, a hydroxy group, a halogen atom, and a carbon number. It represents one of a group consisting of an alkyl group of 1 to 5 or an alkoxy group having 1 to 5 carbon atoms. N 1 and n 2 each independently represent an integer of 0 to 4).
  • Z represents either a linear alkylene group having 2 to 20 carbon atoms or a branched alkylene group having 4 to 20 carbon atoms.
  • the structural unit A 1 is preferably the structural unit A 2 represented by the following formula (16).
  • Y 11 represents one of a group consisting of a benzene ring, a biphenyl ring, a cyclohexane ring, and a bicyclohexane ring which may have a substituent.
  • R 19 and R 20 are independent of each other.
  • N 1 and n 2 each independently represent an integer of 0 to 4.
  • the method for synthesizing the polymer 1 of the present invention is not particularly limited, and the polymer 1 is synthesized by a polymerization method known in the art, for example, a melt polymerization method or a solution polymerization method using a corresponding dicarboxylic acid chloride.
  • a solution polymerization method capable of polymerizing under mild conditions is particularly preferable, and specifically, at least one of the compound of the present invention and the compound having the constituent unit B or the compound having the constituent unit C in the solvent.
  • the seeds may be polycondensed at the interface.
  • the thin film made of the polymer is excellent even if it is subjected to polarized ultraviolet irradiation, obliquely incident ultraviolet irradiation, and heat treatment. Does not show liquid crystal orientation. Since the polymer not containing the structural unit B represented by the formula (3) and the structural unit C represented by the formula (4) has low thermal orientation, it is subjected to polarized ultraviolet irradiation, obliquely incident ultraviolet irradiation, and heat treatment. Even so, the thin film made of the polymer does not show excellent liquid crystal orientation.
  • another aspect of the present invention has a structural unit D represented by the formula (5), and the structural unit B represented by the formula (3) or the structural unit C represented by the formula (4).
  • a polymer having at least one of them (hereinafter referred to as "polymer 2 of the present invention") can be mentioned.
  • the polymer 2 of the present invention is preferably a polymer having a structural unit D represented by the formula (5) and a structural unit B represented by the formula (3).
  • Y 9 and Y 10 are each independently a single bond or -O -, - CO -, - NR 14 -.
  • R 14 is a hydrogen atom Alternatively, it represents one of a group consisting of alkyl groups having 1 to 5 carbon atoms.
  • Ar 3 and Ar 4 each independently represent an aromatic ring having 5 to 7 carbon atoms which may have a substituent. Any carbon atom in the aromatic ring may be replaced with a nitrogen atom, an oxygen atom, and a sulfur atom.
  • R 15 to R 18 are independently hydrogen atom, halogen atom, cyano group, nitro group, and carbon number 1.
  • alkyl group 1-5, the .L 5 which represents one of the group consisting of an alkoxy group having 1 to 5 carbon atoms, a single bond or -O -, - NR 25 -. represents one of the group consisting of wherein, R 25 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • D to f independently represent 0 or 1 respectively.
  • Y 9 and Y 10 are each independently a single bond or -O -, - CO -, - represents one of the group consisting of - NR 14.
  • R 14 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • Y 9 and Y 10 are preferably single bonds or -CO-, -O-.
  • Ar 3 and Ar 4 each independently represent an aromatic ring having 5 to 7 carbon atoms which may have a substituent, and any carbon atom in the aromatic ring can be a nitrogen atom, an oxygen atom, or a sulfur atom. It may be replaced.
  • examples of the substituents in Ar 3 and Ar 4 include a halogen atom, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms, and Ar 3 and Ar 4 do not have a substituent. If it is a hydrogen atom.
  • Ar 3 and Ar 4 are preferably benzene rings which may have a substituent, and more preferably benzene rings.
  • R 15 to R 18 each independently represent one of a group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 5 carbon atoms, and an alkoxy group having 1 to 5 carbon atoms.
  • R 15 ⁇ R 18 is preferably a hydrogen atom.
  • L 5 represents a single bond or -O -, - it represents one of the group consisting of - NR 25.
  • R 25 represents one of a group consisting of a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.
  • L 5 is preferably single bond or —O—.
  • d to f independently represent 0 or 1, respectively.
  • the structural unit D represented by the formula (5) is any of the structural units D-1 to D-5 represented by the following formulas (6) to (10). Is preferable.
  • the method for synthesizing the polymer 2 of the present invention is not particularly limited, and the polymer 2 is synthesized by a polymerization method known in the art, for example, a melt polymerization method or a solution polymerization method using a corresponding dicarboxylic acid chloride.
  • a solution polymerization method capable of polymerizing under mild conditions is particularly preferable, and specifically, among a compound having a structural unit D and a compound having a structural unit B or a compound having a structural unit C in a solvent. Interfacial polycondensation with at least one type may be sufficient.
  • the thin film made of the polymer is excellent even if it is subjected to polarized ultraviolet irradiation, obliquely incident ultraviolet irradiation, and heat treatment. Does not show liquid crystal orientation. Since the polymer not containing the structural unit B represented by the formula (3) and the structural unit C represented by the formula (4) has low thermal orientation, it is subjected to polarized ultraviolet irradiation, obliquely incident ultraviolet irradiation, and heat treatment. Even so, the thin film made of the polymer does not show excellent liquid crystal orientation.
  • the polymers 1 and 2 of the present invention contain other polymers, crystal nucleating agents, surfactants, polyelectrolytes, conductive complexes, inorganic fillers, pigments, antistatic agents, and anti-antistatic agents, as long as the gist of the invention is not exceeded. Blocking agents, lubricants and the like may be blended.
  • the polymers 1 and 2 of the present invention can be used in the form of a thin film. As a result, it exhibits optical characteristics and can be used as an optical thin film (hereinafter referred to as "thin film of the present invention").
  • the method for producing the thin film is not particularly limited, and examples thereof include a melt film forming method and a solution casting method.
  • melt film forming method Specific examples of the melt film forming method include a melt extrusion method using a T-die, a calender molding method, a hot press method, a coextrusion method, a comelt method, a multi-layer extrusion, and an inflation molding method. Not limited.
  • the solution casting method is a method in which a solution in which a polymer is dissolved in a solvent (hereinafter referred to as "casting dope") is cast on a support substrate, and then the solvent is removed by heating or the like to obtain a thin film. ..
  • the spin coating method, the T-die method, the doctor blade method, the bar coater method, and the roll coater method are used as a method of casting the cast dope on the support substrate.
  • the spin coating method, the T-die method, the doctor blade method, the bar coater method, and the roll coater method are used as a method of casting the cast dope on the support substrate.
  • the spin coating method, the T-die method, the doctor blade method, the bar coater method, and the roll coater method are used as a method of casting the cast dope on the support substrate.
  • the most common method is to continuously extrude a casting dope from a die onto a belt-shaped or drum-shaped support substrate.
  • the support substrate used include a glass
  • the thin film of the present invention may contain at least one type of surfactant in order to reduce film thickness unevenness.
  • the surfactant that can be contained include alkyl carboxylate, alkyl phosphate, alkyl sulfonate, fluoroalkyl carboxylate, fluoroalkyl phosphate, fluoroalkyl sulfonate, polyoxyethylene derivative, and fluoro.
  • examples thereof include alkylethylene oxide derivatives, polyethylene glycol derivatives, alkylammonium salts, fluoroalkylammonium salts and the like, and fluorine-containing surfactants are particularly preferable.
  • the thin film of the present invention can be suitably used as an optical thin film, and in particular, since it exhibits a retardation, it can be suitably used as a retardation film.
  • the thin film of the present invention exhibits a phase difference when irradiated with ultraviolet rays.
  • the ultraviolet rays may be polarized ultraviolet rays or obliquely incident ultraviolet rays.
  • the wavelength of ultraviolet rays is preferably 200 nm or more and 400 nm or less. It is preferred as the irradiation energy is 10 mJ / cm 2 or more 10000 mJ / cm 2 or less.
  • the photoreactive groups of the polymers 1 and 2 in the thin film of the present invention preferably have a photoreactivity rate of 50% or less in order to exhibit optical properties.
  • the photoreactivity rate is described, for example, in References Macromolecules 30, 903, 1997. It can be measured by the method described in. More specifically, a general spectrophotometer can be used to measure the transmission spectrum before and after irradiation with ultraviolet light, and the transmission spectrum can be calculated from the spectral change.
  • the thin film of the present invention is further heat-treated after being irradiated with the ultraviolet rays. This causes a phase difference.
  • the heat treatment temperature is preferably a temperature within the range in which the polymers 1 and 2 exhibit liquid crystallinity, and can be exemplified by 50 ° C. or higher and 400 ° C. or lower.
  • the thin film of the present invention can be used as a retardation film by irradiating it with polarized ultraviolet rays or obliquely incident ultraviolet rays and then performing heat treatment to develop three-dimensional refractive index anisotropy.
  • the thin film of the present invention exhibits a retardation, it can be used as a retardation film.
  • a retardation film When used as a retardation film, it may be used as a single film or as a multi-layer film in which other films are laminated.
  • the film laminated on the thin film of the present invention may be the thin film of the present invention, a polymerizable liquid crystal film, a film, a stretched film, or a sputtered film.
  • the thin film of the present invention orients the liquid crystal compound on the film, it can be used as a liquid crystal alignment film.
  • the crude ester product was dissolved in THF (100 ml) at room temperature under a nitrogen stream, and tetrabutylammonium fluoride (20 ml) as a deprotecting agent was added. The mixture was stirred for 1 hour, and the reaction mixture was concentrated under reduced pressure. The residue was redissolved in tetrahydrofuran (THF) and recrystallized from THF / hexane to give 4.16 g of compound. The results of 1 1 H-NMR spectrum are shown below.
  • Example 1 In a three-necked flask equipped with a dropping funnel, 15 ml of water was taken, 1.4 mmol of compound 1 and 4.0 mmol of sodium hydroxide were dissolved and stirred. 0.8 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 1.4 mmol of sebacoil chloride (Compound 22) in 15 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Compound 22 sebacoil chloride
  • Example 2 In a three-necked flask equipped with a dropping funnel, 30 ml of water was taken, 3.0 mmol of compound 2 and 6.0 mmol of sodium hydroxide were dissolved, and the mixture was stirred. 1.2 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 3.0 mmol of sebacoil chloride (Compound 22) in 30 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Compound 22 sebacoil chloride
  • Example 3 In a three-necked flask equipped with a dropping funnel, 9.4 ml of water was taken, 1.9 mmol of compound 2 and 3.8 mmol of sodium hydroxide were dissolved and stirred. 0.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 0.4 mmol of Compound 22 and 1.5 mmol of Compound 23 in 9.4 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 4 In a three-necked flask equipped with a dropping funnel, 30 ml of water was taken, 3.0 mmol of compound 3 and 6.0 mmol of sodium hydroxide were dissolved and stirred. 1.2 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 3.0 mmol of sebacoil chloride (Compound 22) in 30 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 5 In a three-necked flask equipped with a dropping funnel, 10 ml of water was taken, 2.0 mmol of compound 4 and 4.0 mmol of sodium hydroxide were dissolved and stirred. 0.8 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 2.0 mmol of sebacoil chloride (Compound 22) in 10 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Compound 22 sebacoil chloride
  • Example 6 7.5 ml of water was taken in a three-necked flask equipped with a dropping funnel, 1.5 mmol of compound 5 and 3.0 mmol of sodium hydroxide were dissolved and stirred. As a catalyst, 0.6 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 1.5 mmol of sebacoil chloride (Compound 22) in 7.5 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Synbacoil chloride Compound 22
  • Example 7 In a three-necked flask equipped with a dropping funnel, 18.5 ml of water was taken, 0.7 mmol of compound 6 was dissolved, 2.9 mmol of compound 8 and 7.5 mmol of sodium hydroxide were dissolved and stirred. As a catalyst, 1.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 223.7 mmol of compound in 18.5 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 8 In a three-necked flask equipped with a dropping funnel, 18.5 ml of water was taken, 0.7 mmol of compound 6 was dissolved, 2.9 mmol of compound 8 and 7.5 mmol of sodium hydroxide were dissolved and stirred. As a catalyst, 1.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 0.7 mmol of Compound 22 and 2.9 mmol of Compound 23 in 18.5 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 9 18.5 ml of water was taken in a three-necked flask equipped with a dropping funnel, 0.4 mmol of compound 6, 3.3 mmol of compound and 7.5 mmol of sodium hydroxide were dissolved and stirred.
  • a catalyst 1.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added, and the inside of the apparatus was replaced with nitrogen.
  • a solution prepared by dissolving 233.7 mmol of the compound in 18.5 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 10 In a three-necked flask equipped with a dropping funnel, 15.5 ml of water was taken, 0.6 mmol of compound 6 was dissolved, 2.4 mmol of compound 15 and 6.2 mmol of sodium hydroxide were dissolved and stirred. 1.3 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 233.1 mmol of compound in 15.5 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 11 In a three-necked flask equipped with a dropping funnel, 6.0 ml of water was taken, 1.2 mmol of compound 6 and 2.5 mmol of sodium hydroxide were dissolved, and the mixture was stirred. 0.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 1.2 mmol of compound 16 in 18.0 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 12 13.2 ml of water was taken in a three-necked flask equipped with a dropping funnel, 0.6 mmol of compound 6 and 2.0 mmol of compound 8 and 5.3 mmol of sodium hydroxide were dissolved and stirred. 1.1 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 2.1 mmol of compound 23 and 0.5 mmol of compound 16 in 13.2 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 13 13.2 ml of water was taken in a three-necked flask equipped with a dropping funnel, 0.6 mmol of compound 6 and 1.6 mmol of compound 15 and 4.5 mmol of sodium hydroxide were dissolved and stirred. 1.0 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 1.8 mmol of compound 23 and 0.5 mmol of compound 16 in 11.2 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 14 In a three-necked flask equipped with a dropping funnel, 12 ml of water was taken, 0.3 mmol of compound 6 and 2.2 mmol of compound 17 and 4.8 mmol of sodium hydroxide were dissolved and stirred. 1.0 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 232.4 mmol of the compound in 12 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 15 In a three-necked flask equipped with a dropping funnel, 2.2 ml of water was taken, 0.63 mmol of compound 7 and 0.92 mmol of sodium hydroxide were dissolved, and the mixture was stirred. 0.2 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 0.63 mmol of sebacoil chloride (Compound 22) in 2.2 ml of dichloromethane was placed in a dropping funnel, which was added dropwise, and then the mixture was stirred at room temperature for 3 hours.
  • Example 16 14 ml of water was taken in a three-necked flask equipped with a dropping funnel, 0.6 mmol of compound 9, 2.2 mmol of compound 8 and 5.6 mmol of sodium hydroxide were dissolved and stirred. 1.1 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 232.8 mmol of compound in 14 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 17 In a three-necked flask equipped with a dropping funnel, 12 ml of water was taken, 2.4 mmol of compound 9 and 4.8 mmol of sodium hydroxide were dissolved and stirred. 0.9 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 232.4 mmol of the compound in 12 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 18 In a three-necked flask equipped with a dropping funnel, 11.4 ml of water was taken, 10 2.2 mmol of the compound and 4.4 mmol of sodium hydroxide were dissolved and stirred. As a catalyst, 0.6 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 2.2 mmol of compound 22 in 11.4 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 19 In a three-necked flask equipped with a dropping funnel, 10 ml of water was taken, 101.9 mmol of the compound and 3.8 mmol of sodium hydroxide were dissolved, and the mixture was stirred. 0.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 0.4 mmol of Compound 22 and 1.5 mmol of Compound 23 in 10 ml of chloroform was placed in a dropping funnel, which was added dropwise, and then the mixture was stirred at room temperature for 3 hours.
  • Example 20 In a three-necked flask equipped with a dropping funnel, 10 ml of water was taken, 101.9 mmol of the compound and 3.8 mmol of sodium hydroxide were dissolved, and the mixture was stirred. 0.5 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 1.9 mmol of compound in 10 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 21 In a three-necked flask equipped with a dropping funnel, 16 ml of water was taken, 0.3 mmol of compound 11 and 2.8 mmol of compound and 6.4 mmol of sodium hydroxide were dissolved and stirred. 1.3 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 233.2 mmol of the compound in 16 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 22 In a three-necked flask equipped with a dropping funnel, 30.0 ml of water was taken, 0.6 mmol of compound 12 and 2.4 mmol of compound 8 were dissolved in 12.0 mmol of sodium hydroxide, and the mixture was stirred. 2.4 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 3.0 mmol of Compound 23 in 30.0 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 23 In a three-necked flask equipped with a dropping funnel, 30.0 ml of water was taken, 0.6 mmol of compound 13 and 2.4 mmol of compound 8 were dissolved in 12.0 mmol of sodium hydroxide, and the mixture was stirred. 2.4 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 3.0 mmol of Compound 23 in 30.0 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 24 16.8 ml of water was taken in a three-necked flask equipped with a dropping funnel, and 2.1 mmol of compound 14 and 4.2 mmol of sodium hydroxide were dissolved and stirred. 1.3 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 2.1 mmol of Compound 22 in 16.8 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 25 In a three-necked flask equipped with a dropping funnel, 30.0 ml of water was taken, 0.6 mmol of compound 18 and 2.4 mmol of compound 8 were dissolved in 12.0 mmol of sodium hydroxide, and the mixture was stirred. 2.4 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 3.0 mmol of Compound 23 in 30.0 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 26 100 ml of water was taken in a three-necked flask equipped with a dropping funnel, 185 mmol of the compound and 20 mmol of sodium hydroxide were dissolved and stirred. As a catalyst, 4 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 225 mmol of the compound in 50 ml of dichloromethane was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 27 11 ml of water was taken in a three-necked flask equipped with a dropping funnel, and 2.2 mmol of compound 8 and 4.4 mmol of sodium hydroxide were dissolved and stirred. 0.9 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 2.2 mmol of compound 19 in 22 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 28 14 ml of water was taken into a three-necked flask equipped with a dropping funnel, 2.8 mmol of compound 8 and 5.7 mmol of sodium hydroxide were dissolved and stirred. 1.1 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 202.8 mmol of the compound in 28 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 29 30.0 ml of water was taken in a three-necked flask equipped with a dropping funnel, 0.6 mmol of compound 21, 2.4 mmol of compound 8 and 12.0 mmol of sodium hydroxide were dissolved and stirred. 2.4 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 3.0 mmol of Compound 23 in 30.0 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 30 In a three-necked flask equipped with a dropping funnel, 16.5 ml of water was taken, 83.3 mmol of compound and 6.6 mmol of sodium hydroxide were dissolved and stirred. 1.4 ml of a 2.0 wt% aqueous solution of tetra n-butylammonium bromide was added as a catalyst, and the inside of the apparatus was replaced with nitrogen. A solution prepared by dissolving 243.3 mmol of the compound in 16.5 ml of chloroform was placed in a dropping funnel, added dropwise, and then stirred at room temperature for 3 hours.
  • Example 31 6.0% by mass of polymer 3 was dissolved in 94.0% by mass of hexafluoro-2-propanol. This was cast on a quartz substrate, spin-coated at 7000 rpm for 60 seconds, and dried in an oven at 150 ° C. for 30 minutes to obtain a thin film (thickness 1.0 ⁇ m). When the obtained thin film was irradiated with ultraviolet light of 248 nm at an incident angle of 60 degrees at 500 mJ / cm 2 (photoreactivity rate of 50% or less) and then heated at 250 ° C., a high phase difference was exhibited. The phase difference is shown in Table 1.
  • Example 32 3.5% by mass of the polymer 10 was dissolved in 96.5% by mass of hexafluoro-2-propanol. This was cast on a quartz substrate, spin-coated at 4500 rpm for 60 seconds, and dried in an oven at 150 ° C. for 30 minutes to obtain a thin film (thickness 0.5 ⁇ m). When the obtained thin film was irradiated with polarized ultraviolet light of 248 nm at 500 mJ / cm 2 (photoreactivity rate of 50% or less) and then heated at 250 ° C., a high phase difference was exhibited.
  • polarized ultraviolet light 248 nm at 500 mJ / cm 2 (photoreactivity rate of 50% or less
  • Two 25 ⁇ m-thick PET films (manufactured by Toray, product name: Lumirror (R) T60) cut into 1.5 mm x 20 mm are used as spacers, and two quartz plates on which this thin film is laminated are placed inside and the thin film is on the inside.
  • 4-cyano-4'-pentylbiphenyl heated at 50 ° C. was injected into the empty liquid crystal cell to obtain a liquid crystal cell.
  • the obtained liquid crystal cell was observed using a polarizing microscope in three directions so that the angles of the polarizer were 0 °, 45 °, and 90 ° with respect to the direction in which the thin film was irradiated with polarized ultraviolet light. It changed from dark to light to dark, and it was confirmed that the liquid crystal director was evenly aligned and oriented.
  • the liquid crystal director is intended as a vector in the direction in which the long axis of the liquid crystal molecule is oriented (alignment main axis).
  • Example 33 4.2% by mass of the polymer 27 was dissolved in 95.8% by mass of hexafluoro-2-propanol. This was cast on a quartz substrate, spin-coated at 4000 rpm for 60 seconds, and dried in an oven at 150 ° C. for 30 minutes to obtain a thin film (thickness 0.5 ⁇ m). When the obtained thin film was irradiated with polarized ultraviolet light of 248 nm at 500 mJ / cm 2 (photoreactivity rate of 50% or less) and then heated at 250 ° C., a high phase difference was exhibited.
  • polarized ultraviolet light 248 nm at 500 mJ / cm 2 (photoreactivity rate of 50% or less
  • Two 25 ⁇ m-thick PET films (manufactured by Toray, product name: Lumirror (R) T60) cut into 1.5 mm x 20 mm are used as spacers, and two quartz plates on which this thin film is laminated are placed inside and the thin film is on the inside.
  • 4-cyano-4'-pentylbiphenyl heated at 50 ° C. was injected into the empty liquid crystal cell to obtain a liquid crystal cell.
  • the obtained liquid crystal cell was observed using a polarizing microscope in three directions so that the angles of the polarizer were 0 °, 45 °, and 90 ° with respect to the direction in which the thin film was irradiated with polarized ultraviolet light. It changed from dark to light to dark, and it was confirmed that the liquid crystal director was evenly aligned and oriented.
  • Two 25 ⁇ m-thick PET films (manufactured by Toray, product name: Lumirror (R) T60) cut into 1.5 mm x 20 mm are used as spacers, and two quartz plates on which this thin film is laminated are placed inside and the thin film is on the inside.
  • 4-cyano-4'-pentylbiphenyl heated at 50 ° C. was injected into the empty liquid crystal cell to obtain a liquid crystal cell.
  • the obtained liquid crystal cell was observed using a polarizing microscope in three directions so that the angles of the polarizer were 0 °, 45 °, and 90 ° with respect to the direction in which the thin film was irradiated with polarized ultraviolet light. Always remained bright, confirming that the LCD director was not evenly aligned and oriented.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polarising Elements (AREA)
  • Liquid Crystal (AREA)

Abstract

Le but de la présente invention est d'obtenir un film mince optique, qui présente d'excellentes propriétés d'alignement de cristaux liquides, et un film de retard, qui est formé à partir du film mince optique, au moyen d'une irradiation de lumière ultraviolette polarisée ou d'une irradiation de lumière ultraviolette à incidence oblique et d'un traitement thermique sans nécessiter de film d'alignement.　Le but a été atteint au moyen d'un composé représenté par la formule (1). Dans la formule, chacun de X1 à X3 représente un cycle aromatique spécifique ou similaire ; chacun de Y1 et Y2 représente un groupe hydroxy ou similaire ; chacun de Ar1 et Ar2 représente un cycle aromatique spécifique ; chacun de R1 à R4 représente un atome d'hydrogène ou similaire ; chacun de L1 et L4 représente une liaison simple ou similaire ; chacun de L2 et L3 représente une liaison simple ou similaire ; chacun de R7 et R8 représente un atome d'hydrogène ou similaire ; et chacun d'a et b représente 0 ou 1.
PCT/JP2021/006403 2020-02-21 2021-02-19 Composé contenant un groupe photoréactif, polymère et film de retard WO2021167074A1 (fr)

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